2,5-dicyano-3,6-dihydroxy-1,4-benzoquinone | 5312-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-dicyano-3,6-dihydroxy-1,4-benzoquinone
• 英文别名: cyananilic acid；Cyananilsaeure；2,5-Dicyano-3,6-dihydroxy-p-benzoquinone；2,5-dihydroxy-3,6-dioxocyclohexa-1,4-diene-1,4-dicarbonitrile
• CAS: 5312-99-2
• 化学式: C₈H₂N₂O₄
• 分子量: 190.115
• InChiKey: DWUFVOJMPJBOFS-UHFFFAOYSA-N

物化性质

• 沸点：
  344.0±42.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis(pentamethylcyclopentadienyl)iron(II) 、 2,5-dicyano-3,6-dihydroxy-1,4-benzoquinone 以 乙腈 、 苯 为溶剂， 生成 decamethylferrocenium cyananilate
  参考文献：
  名称：

  溴酸，氯苯甲酸和氰基苯甲酸衍生的苯甲酸酯阴离子十甲基二茂铁盐的合成与晶体结构

  摘要：

  使用双（五甲基环戊二烯基）铁Fe（C 5 Me 5）2作为有机金属供体和三个苯甲酸（2,5-二溴-3,6-二羟基-1,4-苯醌），BA，2,5合成了四种配合物-二氯-3,6-二羟基-1,4-苯醌; CA和2,5-二氰基-3,6-二羟基-1,4-苯醌; CNA）作为有机受体。这些配合物具有不同化学计量比[1：1，1：1：1（H 2 O）和2：1]的分子结构已经通过X射线晶体学分析和元素分析确定。这些络合物具有一维交替堆积的排列方式，即⋯D + A − D + A −⋯类型。在1：1组成的结构[Fe（C 5 Me 5）2 ]（BA）（1）中观察到BA单元的溴原子和氧原子之间的紧密接触。有趣的是，结构[Fe（C 5 Me 5）2 ]（CA）（H 2 O）（2）和[Fe（C 5 Me 5）2 ]（CNA）（H 2 O）（3）为1： 1：1（高2O）比包含一维分子带状结构，其中CA或CNA单元与水分子通过O–H

  DOI：

  10.1016/s0020-1693(01)00411-x
• 作为产物：
  描述：

  氰化钾 、 四氯苯醌 在 甲醇 作用下， 生成 2,5-dicyano-3,6-dihydroxy-1,4-benzoquinone
  参考文献：
  名称：

  The occurrence of fatty acids in immature source rocks and their distribution characteristics

  摘要：

  The fatty acids in extractable bitumen and kerogen of immature source racks of the Liaohe Basin and Jiyang sag were investigated in this study. The result showed that the bitumen fatty acids were mainly associated with non-hydrocarbon fraction and that the kerogen fatty acids with some tightly bound fatty acids were mainly bounded in a net structure of kerogen by ester bonds, For the investigated source rocks, the fatty acids in bitumen, bound fatty acids and tightly hound acids in kerogen ranged in 0.01%-0.073 9%, 0.005%-0.045 5% and 0.005%-0.010% respectively. Among the fatty acids analyzed in this study, mono-carboxylic acids, alpha,omega -di-carboxylic acids and hydroxy acids accounted for 70%-100%, 0%-30% and <10% respectively, It was also found that the mono-carboxylic acids with longer chains mainly existed in bitumen, and that the ,omega -di-carboxylic acids and hydroxy acids mainly existed in kerogen, From above, it was assumed that the mono-carboxylic acids in bitumen might have played an important role in the hydrocarbon generation from fatty acids in immature source rocks.

  DOI：

  10.1007/bf03187016

文献信息

• Hydrogen-Bond Interaction in Organic Conductors:  Redox Activation, Molecular Recognition, Structural Regulation, and Proton Transfer in Donor−Acceptor Charge-Transfer Complexes of TTF-Imidazole
  作者：Tsuyoshi Murata、Yasushi Morita、Yumi Yakiyama、Kozo Fukui、Hideki Yamochi、Gunzi Saito、Kazuhiro Nakasuji

  DOI：10.1021/ja072607m

  日期：2007.9.1

  Hydrogen-bond interaction in donor-acceptor charge-transfer complexes of TTF-imidazole demonstrated the electronic effects in terms of control of component ratio and redox activation. These unprecedented effects of hydrogen bonds renewed the criteria giving "a high probability of being organic metals" and produced a number of highly conductive complexes with various acceptors having a wide range of electron-accepting

  TTF-咪唑的供体-受体电荷转移复合物中的氢键相互作用证明了在控制组分比和氧化还原活化方面的电子效应。氢键的这些前所未有的影响更新了“有机金属的可能性很高”的标准，并产生了许多具有各种受电子能力的高导电配合物。在对氯苯醌复合物中，两个分子通过氢键连接并形成 DAD 三联体，将供体-受体组成调节为 2:1。理论计算表明，氢键的极化率控制着供体和对苯醌型受体的氧化还原能力，并在配合物中提供了不同于供体和受体之间氧化还原电位差异所预期的离子性。在对氯苯醌络合物中，这种氢键的电子和结构调控实现了第一个基于氢键功能化 TTF 的金属供体-受体电荷转移络合物。氢键还控制着电荷转移复合物中的分子排列，提供多样化和高度有序的组装结构，对氯苯醌复合物中的 DAD 三元组，I(5) 盐中的一维锯齿形链，氯苯胺酸复合物中的交替供体-受体链和 DADA 环状四聚体在对氨基苯酸复合物中。此外，TTF-咪唑在苯胺酸配
• Development of Organic Conductors with Self-Assembled Architectures of Biomolecules: Synthesis and Crystal Structures of Nucleobase-Functionalized Tetrathiafulvalene Derivatives
  作者：Tsuyoshi Murata、Eigo Miyazaki、Suguru Maki、Yoshikazu Umemoto、Makoto Ohmoto、Kazuhiro Nakasuji、Yasushi Morita

  DOI：10.1246/bcsj.20120102

  日期：2012.9.15

  Supramolecular assemblies and charge-transfer complexes of new nucleobase-functionalized tetrathiafulvalene (TTF) derivatives were investigated. Stille-type cross-coupling reaction between tributylstannylated TTF and iodinated nucleobase derivatives yielded mono- and bisnucleobase-substituted TTF derivatives. The electrochemical measurements revealed that the uracil- and cytosine-substituted derivatives possessed strong electron-donating abilities comparable to that of pristine TTF, and the electron-deficient features of adenine and guanine caused high potential shifts of the oxidation waves. In the solution-state electronic spectra, the intramolecular charge-transfer absorption bands were observed at a low-energy region. In the crystal structures, the donor molecules constructed supramolecular polymers by the complementary hydrogen-bonds inherent in nucleobases; a one-dimensional zigzag chain in the adenine-substituted derivative and a linear chain in the bis(uracil)-substituted derivative. The tetracyanoquinodimethane complexes of uracil- and cytosine-substituted derivatives possessed a mixed valence state exhibiting high conductivities (room-temperature conductivities = 10−2–10−1 S cm−1). In the cyananilic acid complexes, cytosine- and adenine-substituted TTF acted as electron-donors and proton-acceptors to yield simultaneous charge- and proton-transfer complexes.

  研究了新型核苷碱功能化的四硫富瓦烯（TTF）衍生物的超分子聚集体和电荷转移复合物。通过斯蒂尔反应，三正丁基锡化的TTF与碘化核苷碱衍生物之间进行了交叉偶联反应，产生了单核苷碱和双核苷碱取代的TTF衍生物。电化学测量表明，取代有尿嘧啶和胞嘧啶的衍生物具有强的电子给体能力， comparable 于纯净的TTF，而腺嘌呤和鸟嘌呤的电子缺乏特征导致了氧化波的高电位移。在溶液态的电子光谱中，观察到了低能量区域的分子内电荷转移吸收带。在晶体结构中，供体分子通过核苷碱固有的互补氢键构建了超分子聚合物；腺嘌呤取代的衍生物形成了一维之字形链，而二尿嘧啶取代的衍生物形成了一条线性链。取代有尿嘧啶和胞嘧啶的四氰基奎烯和二烯复合物具有混合价态，表现出高电导率（室温电导率 = 10−2–10−1 S cm−1）。在氰苯基酸复合物中，胞嘧啶和腺嘌呤取代的TTF作为电子供体和质子受体，形成了同时进行电荷和质子转移的复合物。
• Synthesis and crystal structures of decamethylferrocenium salts of anilate anions derived from bromanilic acid, chloranilic acid and cyananilic acid
  作者：Md.Badruz Zaman、Masaaki Tomura、Yoshiro Yamashita

  DOI：10.1016/s0020-1693(01)00411-x

  日期：2001.6

  are observed in the structure [Fe(C5Me5)2](BA) (1) of 1:1 composition. Interestingly, the structures [Fe(C5Me5)2](CA)(H2O) (2) and [Fe(C5Me5)2](CNA)(H2O) (3) of 1:1:1(H2O) ratio contain one-dimensional molecular tape structures with the combination of the CA or the CNA units and water molecules via O–H⋯O hydrogen bonds. Different stoichiometric ratios and structures are found from the CNA complexes

  使用双（五甲基环戊二烯基）铁Fe（C 5 Me 5）2作为有机金属供体和三个苯甲酸（2,5-二溴-3,6-二羟基-1,4-苯醌），BA，2,5合成了四种配合物-二氯-3,6-二羟基-1,4-苯醌; CA和2,5-二氰基-3,6-二羟基-1,4-苯醌; CNA）作为有机受体。这些配合物具有不同化学计量比[1：1，1：1：1（H 2 O）和2：1]的分子结构已经通过X射线晶体学分析和元素分析确定。这些络合物具有一维交替堆积的排列方式，即⋯D + A − D + A −⋯类型。在1：1组成的结构[Fe（C 5 Me 5）2 ]（BA）（1）中观察到BA单元的溴原子和氧原子之间的紧密接触。有趣的是，结构[Fe（C 5 Me 5）2 ]（CA）（H 2 O）（2）和[Fe（C 5 Me 5）2 ]（CNA）（H 2 O）（3）为1： 1：1（高2O）比包含一维分子带状结构，其中CA或CNA单元与水分子通过O–H
• The occurrence of fatty acids in immature source rocks and their distribution characteristics
  作者：Jiyang Shi、Mingju Xiang

  DOI：10.1007/bf03187016

  日期：2001.1

  The fatty acids in extractable bitumen and kerogen of immature source racks of the Liaohe Basin and Jiyang sag were investigated in this study. The result showed that the bitumen fatty acids were mainly associated with non-hydrocarbon fraction and that the kerogen fatty acids with some tightly bound fatty acids were mainly bounded in a net structure of kerogen by ester bonds, For the investigated source rocks, the fatty acids in bitumen, bound fatty acids and tightly hound acids in kerogen ranged in 0.01%-0.073 9%, 0.005%-0.045 5% and 0.005%-0.010% respectively. Among the fatty acids analyzed in this study, mono-carboxylic acids, alpha,omega -di-carboxylic acids and hydroxy acids accounted for 70%-100%, 0%-30% and <10% respectively, It was also found that the mono-carboxylic acids with longer chains mainly existed in bitumen, and that the ,omega -di-carboxylic acids and hydroxy acids mainly existed in kerogen, From above, it was assumed that the mono-carboxylic acids in bitumen might have played an important role in the hydrocarbon generation from fatty acids in immature source rocks.